http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1276419-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_966a6c1f382ec9bcb5e3839dfd73e5b8 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/G01D9-30 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J75-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J53-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/G08G1-01 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/G01D18-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/G07C3-12 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/G07C3-12 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/G01D9-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/G07C3-14 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C12P33-08 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J53-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/G07C11-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/G01D1-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/G08G1-01 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07J75-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/G01D9-16 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/G01D18-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/G01D9-30 |
| filingDate | 1970-12-15-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1972-06-01-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1276419-A |
| titleOfInvention | Novel steroids of the pregnane series and a process for the manufacture thereof |
| abstract | 1276419 15#,16#-Methylenesteroids F HOFFMAN-LA ROCHE & CO AG 15 Dec 1970 [17 Dec 1969] 59497/70 Heading C2U Novel compounds have the formula wherein R 6 and R 9 are each H, F, Cl or Br; R 17 and R 21 are each hydroxy or C 1-20 carboxylic acyloxy; and Z is carbonyl or #-hydroxymethylene; and there is an optional double bond in the 1,2-position. Preparations.-(i) 11#-microbial hydroxylation of the corresponding 11-unsubstituted compounds; (ii) treatment of the corresponding #<SP>9(11)</SP>-9,11-unsubstituted compounds with hypochlorous or hypobromous acid to give 9α-(chloro or bromo)-11#-hydroxy products; (iii) treatment of the corresponding 9#,11#-epoxides with HF, HC1 or HBr to give 9α-(chloro, fluoro or bromo) - 11 # - hydroxy products; (iv) dehydration of corresponding 1,2,4,5-saturated-5α-hydroxy-6#-(chloro or bromo) compounds to give #<SP>4</SP>-6-(chloro or bromo) products; (v) oxidation of the corresponding #<SP>4</SP>'<SP>17(20)</SP>-dienes to give #<SP>4-</SP> 17α-hydroxy-20-oxo products; (vi) dehydrohalogenation of the corresponding 1,2,4,5- saturated-5#,6#-di- (chloro or bromo) compounds to give #<SP>4</SP>-6-(chloro or bromo) products; and (vii) hydrolysis of the corresponding 17α,20; 20,21 - bis - (methylenedioxy) compounds to yield 17α-hydroxy-20-oxo products. Product interconversions.-(i) 6-halogenation of #<SP>4</SP>-3-oxo-6-unsubstituted compounds or 3- enol ethers thereof; (ii) 1,2-dehydrogenation of 1,2-saturated compounds; (iii) acylation of 17-/21-hydroxy groups; (iv) hydrolysis of 17-/21-acyloxy groups; (v) reduction of 11-oxo to 11 #-hydroxy (with intermediate protection of the 3- and 20-oxo-groups) and (vi) oxidation of 11#-hydroxy to 11-oxo (with intermediate protection of any 17- or 21-hydroxy group). Intermediates.-21 - Acetoxy - 17α - hydroxy- 15#,16# - methylene - pregna - 4,9(11) - diene- 3,20-dione is prepared by dehydration of the corresponding 9-hydro-11#-ol. 21 - Acetoxy - 9#,11# - epoxy - 17α - hydroxy- 15#,16# - methylene - pregn - 4 - ene - 3,20 - dione is prepared from the corresponding 9α-bromo- 11#-ol by the action of sodium acetate in acetone. 21 - Acetoxy - 3 - ethoxy - 9α -fluoro - 11#,17α- dihydroxy - 15#,16# - methylenepregna - 3,5 - dien- 20-one is prepared from the corresponding 4-ene.3,20-dione by the action of ethyl orthoformate. 6α - Fluoro - 17α,21 - dihydroxy - 15#,16#- methylenepregn - 4 - ene - 3,20 - dione (XVI) is prepared from the corresponding 6-dehalo compound (XV) by the sequence: XV # 21- acetoxy . 17α - hydroxy - 15#,16# - methylenepregn - 4 - ene - 3,20 - dione # 21 - acetoxy- 17α - hydroxy - 3 - methoxy - 15#,16# - methylenepregna - 3,5 - dien - 20 - one # 21 - acetoxy- 6α - fluoro - 17α - hydroxy - 15#,16# - methylenepregn - 4 - ene - 3,20 - dione (+ the 6# - fluoro epimer thereof) # XVI. 9α - Fluoro - 11# - hydroxy - 15#,16# - methylene - 17,20; 20,21 - bis - (methylenedioxy) - pregn- 4-en-3-one (XVIII) is prepared from 11#,17α,21- trihydroxy - 15#,16# - methylenepregn - 4 - ene- 3,20-dione (XVII) by the sequence: XVII# 15#,16# - methylene - 17,20; 20,21 - bis - (methylenedioxy) - 11# - hydroxypregn - 4 - en - 3 - one # 15#,16# - methylene - 17,20; 20,21 - bis- (methylenedioxy) pregna - 4,9(11) - dien - 3 - one # 9α - bromo - 11# - hydroxy - 15#,16# - methylene - 17,20; 20,21 - bis - (methylenedioxy) pregn- 4 - en - 3 - one # 17,20; 20,21 - bis - (methylene. dioxy) - 9#,11# - epoxy - 15#,16# - methylenepregn- 4-en-3-one # XVIII. Anti-inflammatory compositions for oral, parenteral, topical or rectal administration comprise a compound of the above formula and a carrier. |
| priorityDate | 1969-12-17-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 48.